IE65869B1 - Process for the preparation of sulphinylpristinamycin 11B - Google Patents

Process for the preparation of sulphinylpristinamycin 11B

Info

Publication number: IE65869B1
Authority: IE; Ireland
Prior art keywords: formula; pristinamycin; equivalents; pct; hydrogen peroxide
Prior art date: 1990-07-16

Application number

IE244791A

Other languages

English (en)

Other versions

IE912447A1 (en

Inventor

Xavier Radisson

Original Assignee

Rhone Poulenc Rorer Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-07-16

Filing date

1991-07-12

Publication date

1995-11-29

1991-07-12 Application filed by Rhone Poulenc Rorer Sa filed Critical Rhone Poulenc Rorer Sa

1992-01-29 Publication of IE912447A1 publication Critical patent/IE912447A1/en

1995-11-29 Publication of IE65869B1 publication Critical patent/IE65869B1/en

Links

238000002360 preparation method Methods 0.000 title claims abstract description 4
238000000034 method Methods 0.000 title claims description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 16
JOOMGSFOCRDAHL-XKCHLWDXSA-N pristinamycin-IIB Natural products CC(C)[C@@H]1OC(=O)[C@H]2CCCN2C(=O)c3coc(CC(=O)C[C@@H](O)C=C(C)C=CCNC(=O)C=C[C@H]1C)n3 JOOMGSFOCRDAHL-XKCHLWDXSA-N 0.000 claims abstract description 7
230000001476 alcoholic effect Effects 0.000 claims abstract description 4
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 claims abstract description 3
229960003961 pristinamycin Drugs 0.000 claims description 7
YVMBAUWDIGJRNY-BESUKNQGSA-N 4o8o7q7iu4 Chemical compound C1C(=O)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@@H](C)[C@@H](C(C)C)OC(=O)C2=CCCN2C(=O)C2=COC1=N2.N([C@@H]1C(=O)N[C@@H](C(N2CCC[C@H]2C(=O)N(C)[C@@H](CC=2C=CC(=CC=2)N(C)C)C(=O)N2CCC(=O)C[C@H]2C(=O)N[C@H](C(=O)O[C@@H]1C)C=1C=CC=CC=1)=O)CC)C(=O)C1=NC=CC=C1O YVMBAUWDIGJRNY-BESUKNQGSA-N 0.000 claims description 6
RLNUPSVMIYRZSM-UHFFFAOYSA-N Pristinamycin Natural products CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC(=CC=2)N(C)C)CCN(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O RLNUPSVMIYRZSM-UHFFFAOYSA-N 0.000 claims description 5
108010079780 Pristinamycin Proteins 0.000 claims description 5
DAIKHDNSXMZDCU-OUDXUNEISA-N pristinamycin-IIA Natural products CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c3coc(CC(=O)C[C@H](O)C=C(C)C=CCNC(=O)C=C[C@@H]1C)n3 DAIKHDNSXMZDCU-OUDXUNEISA-N 0.000 claims description 5
-1 sulphinyl Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
230000001590 oxidative effect Effects 0.000 claims 1
150000002978 peroxides Chemical class 0.000 claims 1
230000003647 oxidation Effects 0.000 abstract description 6
238000007254 oxidation reaction Methods 0.000 abstract description 6
125000000217 alkyl group Chemical group 0.000 abstract description 3
108010015791 Streptogramin A Proteins 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
150000003568 thioethers Chemical class 0.000 description 3
QWMFKVNJIYNWII-UHFFFAOYSA-N 5-bromo-2-(2,5-dimethylpyrrol-1-yl)pyridine Chemical compound CC1=CC=C(C)N1C1=CC=C(Br)C=N1 QWMFKVNJIYNWII-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
101000840267 Homo sapiens Immunoglobulin lambda-like polypeptide 1 Proteins 0.000 description 1
102100029616 Immunoglobulin lambda-like polypeptide 1 Human genes 0.000 description 1
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000004966 inorganic peroxy acids Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06182—Dipeptides with the first amino acid being heterocyclic and Pristinamycin II; Derivatives thereof

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Biophysics (AREA)
Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Cephalosporin Compounds (AREA)
Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Investigating Or Analysing Biological Materials (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

IE244791A 1990-07-16 1991-07-12 Process for the preparation of sulphinylpristinamycin 11B IE65869B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9009034A FR2664598A1 (fr)	1990-07-16	1990-07-16	Procede de preparation de sulfinyl pristinamycine iib.

Publications (2)

Publication Number	Publication Date
IE912447A1 IE912447A1 (en)	1992-01-29
IE65869B1 true IE65869B1 (en)	1995-11-29

Family

ID=9398752

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE244791A IE65869B1 (en)	1990-07-16	1991-07-12	Process for the preparation of sulphinylpristinamycin 11B

Country Status (18)

Country	Link
US (1)	US5326862A (fr)
EP (1)	EP0539450B1 (fr)
JP (1)	JP3345812B2 (fr)
KR (1)	KR100199067B1 (fr)
AT (1)	ATE103606T1 (fr)
AU (1)	AU641538B2 (fr)
CA (1)	CA2086924C (fr)
DE (1)	DE69101555T2 (fr)
DK (1)	DK0539450T3 (fr)
ES (1)	ES2062807T3 (fr)
FI (1)	FI100885B (fr)
FR (1)	FR2664598A1 (fr)
IE (1)	IE65869B1 (fr)
IL (1)	IL98852A (fr)
NZ (1)	NZ238950A (fr)
PT (1)	PT98335B (fr)
WO (1)	WO1992001693A1 (fr)
ZA (1)	ZA915444B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1995020590A1 (fr) *	1994-01-27	1995-08-03	The Trustees Of Columbia University In The City Of New York	Recepteurs enantioselectifs pour derives d'acide amine et autres composes
JP3338876B2 (ja) *	1996-03-28	2002-10-28	住友精化株式会社	α−ハロアセトフェノン誘導体の製造方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2576022B1 (fr) *	1985-01-11	1987-09-11	Rhone Poulenc Sante	Nouveaux derives de la pristinamycine ii b, leur preparation et les compositions pharmaceutiques qui les contiennent
GB8616768D0 (en) *	1986-07-09	1986-08-13	May & Baker Ltd	Process
AU593363B2 (en) *	1987-07-07	1990-02-08	Rhone-Poulenc Sante	Process for preparation of pristinamycin 11b derivatives
GB2206879A (en) *	1987-07-07	1989-01-18	May & Baker Ltd	Novel pristinamycin IIB derivatives, their preparation and pharmaceutical compositions containing them
GB2206577B (en) *	1987-07-07	1990-10-24	May & Baker Ltd	New process for the preparation of therapeutically useful pristinamycin iib sulphone derivatives
FR2664600B1 (fr) *	1990-07-16	1994-09-02	Rhone Poulenc Sante	Nouveau sel derive de la dialcoylaminoalcoyl-sulfonyl-26 pristinamycine iib.
FR2664597B1 (fr) *	1990-07-16	1994-09-02	Rhone Poulenc Sante	Procede de preparation de sulfonylpristinamycine iib.

1990
- 1990-07-16 FR FR9009034A patent/FR2664598A1/fr active Granted
1991
- 1991-07-12 NZ NZ238950A patent/NZ238950A/en unknown
- 1991-07-12 IE IE244791A patent/IE65869B1/en not_active IP Right Cessation
- 1991-07-12 ZA ZA915444A patent/ZA915444B/xx unknown
- 1991-07-15 AT AT91913246T patent/ATE103606T1/de not_active IP Right Cessation
- 1991-07-15 ES ES91913246T patent/ES2062807T3/es not_active Expired - Lifetime
- 1991-07-15 KR KR1019930700114A patent/KR100199067B1/ko not_active Expired - Fee Related
- 1991-07-15 AU AU82845/91A patent/AU641538B2/en not_active Ceased
- 1991-07-15 DE DE69101555T patent/DE69101555T2/de not_active Expired - Fee Related
- 1991-07-15 WO PCT/FR1991/000580 patent/WO1992001693A1/fr not_active Ceased
- 1991-07-15 JP JP51254691A patent/JP3345812B2/ja not_active Expired - Fee Related
- 1991-07-15 EP EP91913246A patent/EP0539450B1/fr not_active Expired - Lifetime
- 1991-07-15 IL IL9885291A patent/IL98852A/en not_active IP Right Cessation
- 1991-07-15 CA CA002086924A patent/CA2086924C/fr not_active Expired - Fee Related
- 1991-07-15 DK DK91913246.4T patent/DK0539450T3/da active
- 1991-07-15 US US07/961,926 patent/US5326862A/en not_active Expired - Fee Related
- 1991-07-16 PT PT98335A patent/PT98335B/pt not_active IP Right Cessation
1992
- 1992-12-11 FI FI925644A patent/FI100885B/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
PT98335A (pt)	1992-06-30
FR2664598A1 (fr)	1992-01-17
AU641538B2 (en)	1993-09-23
FR2664598B1 (fr)	1994-07-13
EP0539450B1 (fr)	1994-03-30
DE69101555D1 (de)	1994-05-05
FI925644A0 (fi)	1992-12-11
FI925644L (fi)	1992-12-11
DK0539450T3 (da)	1994-05-09
PT98335B (pt)	1999-01-29
WO1992001693A1 (fr)	1992-02-06
ZA915444B (en)	1992-04-29
EP0539450A1 (fr)	1993-05-05
IL98852A0 (en)	1992-07-15
IL98852A (en)	1995-05-26
CA2086924C (fr)	1999-09-14
CA2086924A1 (fr)	1992-01-17
ATE103606T1 (de)	1994-04-15
JP3345812B2 (ja)	2002-11-18
JPH05508410A (ja)	1993-11-25
KR100199067B1 (ko)	1999-06-15
FI100885B (fi)	1998-03-13
US5326862A (en)	1994-07-05
AU8284591A (en)	1992-02-18
ES2062807T3 (es)	1994-12-16
IE912447A1 (en)	1992-01-29
NZ238950A (en)	1992-09-25
DE69101555T2 (de)	1994-07-28

Legal Events

Date	Code	Title	Description
2005-04-06	MM4A	Patent lapsed

Publication	Publication Date	Title
FR2600650A1 (fr)	1987-12-31	Procede de preparation d'imidazopyridines et composes intermediaires
Minisci et al.	1989	A new general method of homolytic alkylation of protonated heteroaromatic bases by carboxylic acids and iodosobenzene diacetate
Ravikumar et al.	1998	Role of hexafluoro‐2‐propanol in selective oxidation of sulfide to sulfoxide: efficient preparation of glycosyl sulfoxides
JPH04112877A (ja)	1992-04-14	新規シアノピラジン誘導体及びその製造方法
IE65869B1 (en)	1995-11-29	Process for the preparation of sulphinylpristinamycin 11B
CN102939298B (zh)	2015-11-25	制备蝶啶衍生物的方法
FI86303C (fi)	1992-08-10	Foerbaettrat foerfarande foer framstaellning av aminoalkylsulfonyl-pristinamycin iib -derivat.
Jones et al.	1966	STEROIDS AND STEROIDASES: III. DICYCLOHEXYLCARBODIIMIDE–DIMETHYL SULFOXIDE OXIDATIONS OF ALCOHOLS AND THIOLS
CS212343B2 (en)	1982-03-26	Method of oxidation of penicillines
US5272266A (en)	1993-12-21	Vinylsulphonylpristinamycin and its preparation
Balicki et al.	1992	A mild and facile preparation of sulfoxides from sulfides by use of the H2O2‐urea/phthalic anhydride system
Silverman	1981	Mechanism of isomerization of a. beta.-keto sulfide
EP0298177A1 (fr)	1989-01-11	Nouveau procédé de préparation de dérivés de la pristinamycine IIB
US5347001A (en)	1994-09-13	Process for preparing sulphonylpristinamycin IIB
EP0117861B1 (fr)	1987-12-09	Procédé d'obtention de la vincristine
GB2206577A (en)	1989-01-11	New process for the preparation of therapeutically useful pristinamycin IIB sulphone derivatives
US4792610A (en)	1988-12-20	Process for the preparation of 5-phenylsulfinyl-1H-2-(methoxycarbonylamino)-benzimidazole
KR890000522B1 (ko)	1989-03-20	페니실란산 1,1-디옥사이드의 제조방법
IE922329A1 (en)	1993-01-27	PROCESS FOR THE PREPARATION OF¹17b-SUBSTITUTED-4-AZA-5a-ANDROSTAN-3-ONE DERIVATIVES
IL123617A (en)	2001-01-11	Process for the purification of diphenyl ether compounds
KR950010082B1 (ko)	1995-09-06	프리스티나마이신 ⅱ_b 유도체의 제조 방법
Hanlon et al.	1986	Aspects of the chemistry of 6-diazopenicillanate S-oxide and S, S-dioxide
KR960010101B1 (ko)	1996-07-25	4-오르소토릴티오세미카바지드의 제조방법
KR20010029475A (ko)	2001-04-06	약제학적 화합물의 제조 방법
Denerley et al.	1979	Preparation of secopenicillanates; preparation of methyl 3-methyl-2-[(2 R, 3 R)-2-methylthio-4-oxo-3-phthalimidoazetidin-1-yl] but-2-enoate